NP-MRD: Showing NP-Card for (1s,2s,5s,14s,15r,18r,19s)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁷,¹²]pentacosa-7,9,11-trien-20-one (NP0236008)

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Record Information

Version

2.0

Created at

2022-09-06 18:48:07 UTC

Updated at

2022-09-06 18:48:07 UTC

NP-MRD ID

NP0236008

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,5s,14s,15r,18r,19s)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁷,¹²]pentacosa-7,9,11-trien-20-one

Description

(1S,2S,5S,14S,15R,18R,19S)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁷,¹²]Pentacosa-7,9,11-trien-20-one belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring. (1s,2s,5s,14s,15r,18r,19s)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁷,¹²]pentacosa-7,9,11-trien-20-one is found in Petrosia durissima. Based on a literature review very few articles have been published on (1S,2S,5S,14S,15R,18R,19S)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁷,¹²]Pentacosa-7,9,11-trien-20-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062220482D          

 31 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309062220482D          

 31 36  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0236008

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2O[C@@]3(C)CC[C@H]4[C@@](C)(CC[C@H]5[C@]6(C)CCC[C@]45COC6=O)[C@@H]3CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O4/c1-24-12-8-21-25(2)10-5-11-27(21,16-30-23(25)28)20(24)9-13-26(3)22(24)15-17-14-18(29-4)6-7-19(17)31-26/h6-7,14,20-22H,5,8-13,15-16H2,1-4H3/t20-,21-,22-,24+,25-,26-,27-/m0/s1

> <INCHI_KEY>
PTWKRUJSHFVLJF-GVVWVFJASA-N

> <FORMULA>
C27H36O4

> <MOLECULAR_WEIGHT>
424.581

> <EXACT_MASS>
424.261359639

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
48.87962997049057

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5S,14S,15R,18R,19S)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0^{1,18}.0^{2,15}.0^{5,14}.0^{7,12}]pentacosa-7,9,11-trien-20-one

> <JCHEM_LOGP>
5.469302396000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.531954992672045

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
118.71399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,14S,15R,18R,19S)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0^{1,18}.0^{2,15}.0^{5,14}.0^{7,12}]pentacosa-7,9,11-trien-20-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      15.329  -2.005   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      13.816  -2.290   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.813  -1.122   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.323   0.331   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.319   1.500   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.806   1.215   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.296  -0.238   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.299  -1.407   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.782  -0.523   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.779   0.645   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.289   2.098   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.799   3.551   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.286   3.266   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.772   2.981   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.262   1.528   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.749   1.243   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.236   1.534   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.962   0.670   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.671  -0.842   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.535  -2.117   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.688  -3.403   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.047  -2.408   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.357  -3.916   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.240  -1.971   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.613  -0.031   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.239  -0.210   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.242  -1.378   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.756  -1.093   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.266   0.360   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.269  -0.808   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.802   2.383   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   29                                                  
CONECT   11   10   12   13   31                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   29                                                  
CONECT   16   15   17   25   26                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   26                                             
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   16                                                       
CONECT   26   20   16   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   10   15   30                                             
CONECT   30   29                                                            
CONECT   31   11    6                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₆O₄

Average Mass

424.5810 Da

Monoisotopic Mass

424.26136 Da

IUPAC Name

(1S,2S,5S,14S,15R,18R,19S)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0^{1,18}.0^{2,15}.0^{5,14}.0^{7,12}]pentacosa-7,9,11-trien-20-one

Traditional Name

(1S,2S,5S,14S,15R,18R,19S)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0^{1,18}.0^{2,15}.0^{5,14}.0^{7,12}]pentacosa-7,9,11-trien-20-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2O[C@@]3(C)CC[C@H]4[C@@](C)(CC[C@H]5[C@]6(C)CCC[C@]45COC6=O)[C@@H]3CC2=C1

InChI Identifier

InChI=1S/C27H36O4/c1-24-12-8-21-25(2)10-5-11-27(21,16-30-23(25)28)20(24)9-13-26(3)22(24)15-17-14-18(29-4)6-7-19(17)31-26/h6-7,14,20-22H,5,8-13,15-16H2,1-4H3/t20-,21-,22-,24+,25-,26-,27-/m0/s1

InChI Key

PTWKRUJSHFVLJF-GVVWVFJASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Petrosia durissima	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthenes

Alternative Parents

Substituents

Naphthopyran
Xanthene
Naphthalene
Anisole
Delta valerolactone
Delta_valerolactone
Alkyl aryl ether
Benzenoid
Pyran
Oxane
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.47	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	118.71 m³·mol⁻¹	ChemAxon
Polarizability	48.88 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10185823

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11316222

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,5s,14s,15r,18r,19s)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁷,¹²]pentacosa-7,9,11-trien-20-one (NP0236008)

MOL for NP0236008 ((1s,2s,5s,14s,15r,18r,19s)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁷,¹²]pentacosa-7,9,11-trien-20-one)

3D MOL for NP0236008 ((1s,2s,5s,14s,15r,18r,19s)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁷,¹²]pentacosa-7,9,11-trien-20-one)

3D SDF for NP0236008 ((1s,2s,5s,14s,15r,18r,19s)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁷,¹²]pentacosa-7,9,11-trien-20-one)

3D-SDF for NP0236008 ((1s,2s,5s,14s,15r,18r,19s)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁷,¹²]pentacosa-7,9,11-trien-20-one)

PDB for NP0236008 ((1s,2s,5s,14s,15r,18r,19s)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁷,¹²]pentacosa-7,9,11-trien-20-one)

3D PDB for NP0236008 ((1s,2s,5s,14s,15r,18r,19s)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁷,¹²]pentacosa-7,9,11-trien-20-one)

SMILES for NP0236008 ((1s,2s,5s,14s,15r,18r,19s)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁷,¹²]pentacosa-7,9,11-trien-20-one)

INCHI for NP0236008 ((1s,2s,5s,14s,15r,18r,19s)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁷,¹²]pentacosa-7,9,11-trien-20-one)

Structure for NP0236008 ((1s,2s,5s,14s,15r,18r,19s)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁷,¹²]pentacosa-7,9,11-trien-20-one)

3D Structure for NP0236008 ((1s,2s,5s,14s,15r,18r,19s)-10-methoxy-5,15,19-trimethyl-6,21-dioxahexacyclo[17.3.3.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁷,¹²]pentacosa-7,9,11-trien-20-one)